Problems receiving mail from GMail – STARTTLS is a bad idea

A couple of weeks ago, users started complaining that people using GMAIL (and possibly iCloud) were having their emails bounced back to them from my servers. This is odd – most complaints on the Internet are from users of dodgy hosting companies having their mail rejected by GMail as likely spam. But I haven’t blacklisted Google, and all other mail is working, so they must have been mistaken.

But as soon as I could, I tried it for myself. And sure enough, a bounce came back. The relevent bit is:

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Oh my! The STARTTLS stuff isn’t working because there’s no shared cypher! Hang on a minute, there isn’t supposed to be. Who told Google they could use STARTTLS on port 25. It’d be neat if it worked, but it’s not configured – at least not with a certificate from a public CA. It actually works just fine if you are cool with self-signed (private) certificates. So what is Google playing at?

In the wake of Edward Snowden, people have started worrying about this kind of thing, so companies like Google are trying to be seen doing something about it, and encrypting mail might seem like a good idea. Unfortunately STARTTLS is a bad idea. The rationale behind STARTTLS was to add encryption to a previously unencrypted port’s traffic. If the sender issued a STARTTLS as part of the protocol it could switch in to TLS mode if it knew how; otherwise it would just work as normal. The IETF was very keen on this in the late 1990’s as an easy fix, citing all sorts of iffy reasons, generally to do with having two ports; one standard and one encrypted. They thought it would be confusing, requiring different URLs and not allow for opportunistic automatic encryption of the kind Google seems to be attempting.

As far as I’m concerned, this is rubbish. Having clearly defined encrypted and unencrypted ports means you know where you are. It either is or it isn’t. If you say something must be encrypted, turn off the unencrypted port. STARTTLS allows a fall-back to plain text if you specify the clear text port; and if you have a man-in-the-middle you’ll never know that the STARTTLS was stripped from the negotiations. It opens up a vulnerability that need not be there, all for the sake of saving a port. And time is on my side in this argument. Since 1999 the implementation of encrypted ports has really taken off, with https, smtps (in spite of 465 being rescinded), imaps – you name it – all servers and clients support it and you know where you are.

So what’s this sudden clamouring for the insecure STARTTLS? Naivety on the part of the large internet companies, or a plot to make people think their email traffic is now safe from snoopers when its not?

I’ve reported this problem and I await an answer from Google, but my best guess is that they’re speculatively using STARTTLS, and then barfing and throwing their toys from the pram when it doesn’t work because the verify can’t be done. Having thought about it, I’m okay with the idea of trying STARTTLS as long as you don’t mind about the CA used for the certificate; and if you can’t negotiate a TLS link, go back to plain text. In many ways it’d be better to use the well known port 465 for TLS, and if it can’t be opened, go to plain text on 25. Except there’s no guarantee that port 465 is on the same server as port 25, and it’s normally configured to require SASL authentication. As everyone knows, apart from Google it seems, assumption is the mother of all foul-ups.

Encryption is a good idea, but making assumptions about Port 25 being anything other that straight SMTP is asking for trouble.